Cucurbit[8]uril-Based Supramolecular Probe for the Detection of 3-Nitrotyrosine in Human Serum and Plasma

ACS Sens. 2024 Jan 26;9(1):424-432. doi: 10.1021/acssensors.3c02211. Epub 2024 Jan 12.

Abstract

The biomarker 3-nitrotyrosine (3-NT) is widely recognized as an indicator of renal oxidative stress injury, making its detection crucial for the early identification of renal insufficiency. This study presents the design and synthesis of a tetraphenylstyrene imidazole derivative (TIPE-MI), which is utilized to create a supramolecular probe in conjunction with cucurbit[8]uril (Q[8]) through host-guest interactions. The resulting supramolecular self-assembly exhibits excellent optical properties and has been employed for the specific detection of 3-NT through fluorescence quenching. The introduction of 3-NT resulted in a decreased fluorescence intensity of the yellow fluorescent probe, which gradually transitioned from bright yellow to light yellow and then became colorless as the 3-NT concentration was increased. A portable detection platform was devised to augment the efficiency of detection. In order to facilitate biological applications, we have substantiated the probe's exceptional precision in detecting 3-NT in biological samples, encompassing human serum and plasma. The probe also exhibited negligible cytotoxicity. The accumulation of the probe in renal cells elicited a fluorescence signal, thereby indicating the prospective viability of this system for visual detection with renal cytocompatibility.

Keywords: 3-nitrotyrosine; cell imaging; host−guest; kidney injury; supramolecular probe.

MeSH terms

  • Bridged-Ring Compounds*
  • Fluorescent Dyes*
  • Humans
  • Prospective Studies
  • Spectrometry, Fluorescence
  • Tyrosine / analogs & derivatives*

Substances

  • 3-nitrotyrosine
  • Bridged-Ring Compounds
  • Fluorescent Dyes
  • Tyrosine